Make Room For A Free Croissant

My favorite movie as a kid was The Princess Bride.

I watched it so many times I could recite entire scenes from memory. Still can. But the line that lodged itself deepest wasn't the romance or the sword fights or the mostly dead. It was Westley, looking at Buttercup and saying,

"Life is pain, highness. Anyone who says differently is selling something."

Now, pair that with my favorite book growing up, the Bible, and the Apostle Paul saying to the Romans:

"We glory in our sufferings, because we know that suffering produces perseverance; perseverance, character; and character, hope."

My point of view on life was shaped before I even knew it. And definitely before I learned that the Stoics lived it and that the Buddha taught it.

We are all learning, some faster than others, that discomfort is no longer optional.

From my very first job out of college, I was paid on commission. No base. No guarantee. If I didn't sell, I didn't eat. And that happened a couple of times. Waiting for the next commission check to clear. And later, even when things were going well, I was always scanning the horizon. Not out of anxiety, out of training. The Princess Bride and life had prepared me. I believed the comfort was temporary. Every up had a down waiting behind it.

That's been true through every chapter. And it is even right now at Stretch. I recruited an executive team, told them exactly how much runway we had, and watched them choose to join anyway. No false promises. Just: here's the reality, here's what we're building, here's what we have to do with limited resources and not enough time. They still came. That's the team I want.

My career feels like it has been spent with a gun to my head about the next sale, the next commission tier, the next round of capital. You learn to develop a relationship with uncertainty that most people never get. Not fearlessness, let’s be clear about that. I've been scared more times than I can count. But familiarity. A quiet confidence that says, I've been here before, and I'll figure it out again.  

The question I keep sitting with is, how do you get that without the gun?

Because most people are waiting for the crisis to use that muscle. And by then, it's too late to train. You're already in the fight.

A few weeks ago, a member of the League of Gentlemen asked me that exact question. This particular member is talented, hungry, and can see the life he wants to build. But the next stage of his path runs straight through a lot of discomfort he hasn't experienced yet. He asked me: How do I get comfortable with this?

I told him about my relationship with rejection.

Not the philosophy of it. My practice.

I asked him where he gets his coffee in the morning. He told me the name of the shop. I asked if they had a pastry case. He said yes. I told him: tomorrow morning, walk in and ask for a free croissant. Ask like you expect it to happen. Ask as if it hasn't even occurred to you that they would say no. And then, when they look at you funny, or say no, notice that you're still standing. Notice that nothing actually broke.

That's the training. Small, daily, deliberate moments of rejection until the word loses its teeth.

I used to do this at every rental car counter and hotel check-in. It hardly ever worked, but it got me my daily dose of rejection and the reminder that you never know unless you ask. 

Epictetus put it plainly:

"It is not things themselves that trouble people, but their judgments about those things."

The croissant isn't the point. The rental car update isn’t what matters. The story you tell yourself when someone says no, that's what you're actually practicing. That's where the perseverance into character that Paul was talking about gets built. One small "no" at a time.

Most people are building lives designed to never test whether they can handle hard things. And that works, until it doesn't.

The ones I've watched navigate real uncertainty, not just talk about it, but actually live inside it, they've all got something in common. Not toughness. Familiarity. They've been uncomfortable before. They figured it out. And that proof lives somewhere in their chest that no one can take away.

Life is pain, Highness.

But suffering produces perseverance. Perseverance produces character. And character produces hope.

We are all enrolled in this class now. Go ask for that croissant.